6-hydroxy-8-methyl-2(1H)-quinolinone | 143268-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-hydroxy-8-methyl-2(1H)-quinolinone
• 英文别名: 6-hydroxy-8-methylcarbostyril；6-Hydroxy-8-methylquinolin-2(1H)-one；6-hydroxy-8-methyl-1H-quinolin-2-one
• CAS: 143268-86-4
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: XKIKBJPZUYXYOL-UHFFFAOYSA-N

物化性质

• 沸点：
  431.3±45.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hydroxy-8-methyl-2(1H)-quinolinone 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 6-[3-(3,4-Dimethoxy-benzylamino)-2-hydroxy-propoxy]-8-methyl-1H-quinolin-2-one
  参考文献：
  名称：

  Novel positive inotropic agents: synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives

  摘要：

  A series of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinones has been synthesized and evaluated for positive inotropic activity on the canine heart. Some of these derivatives have a potent activity with none or negative chronotropic effect in isolated, blood-perfused dog heart preparations. They also display a high selectivity for positive inotropic effect over chronotropic and vasodilatory effects in anesthetized dogs. (+/-)-6-[2-Hydroxy-3-[(3-methoxybenzyl)amino]propoxy]-2(1H)-quinolinone (39) and (+/-)-6-[3-(3,4-dimethoxybenzyl)amino]-2-hydroxypropoxy]-2(1H)-quinolinone (40) were further investigated in conscious dogs. After iv administration, they did not affect heart rate or mean blood pressure at the dose producing a 50% increase in the peak of the first derivative of the left ventricular pressure. The compounds (39,OPC-18750, and 40,OPC-18790) are the most promising agents with desirable biological activities, and now are currently undergoing clinical evaluation.

  DOI：

  10.1021/jm00098a003
• 作为产物：
  描述：

  2-甲基-4-甲氧基苯胺 在 三氯化铝 、 potassium carbonate 作用下， 以 水 、 氯苯 、 丙酮 为溶剂， 反应 3.5h， 生成 6-hydroxy-8-methyl-2(1H)-quinolinone
  参考文献：
  名称：

  Novel positive inotropic agents: synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives

  摘要：

  A series of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinones has been synthesized and evaluated for positive inotropic activity on the canine heart. Some of these derivatives have a potent activity with none or negative chronotropic effect in isolated, blood-perfused dog heart preparations. They also display a high selectivity for positive inotropic effect over chronotropic and vasodilatory effects in anesthetized dogs. (+/-)-6-[2-Hydroxy-3-[(3-methoxybenzyl)amino]propoxy]-2(1H)-quinolinone (39) and (+/-)-6-[3-(3,4-dimethoxybenzyl)amino]-2-hydroxypropoxy]-2(1H)-quinolinone (40) were further investigated in conscious dogs. After iv administration, they did not affect heart rate or mean blood pressure at the dose producing a 50% increase in the peak of the first derivative of the left ventricular pressure. The compounds (39,OPC-18750, and 40,OPC-18790) are the most promising agents with desirable biological activities, and now are currently undergoing clinical evaluation.

  DOI：

  10.1021/jm00098a003

文献信息

• Quinoline derivatives or salt thereof and remedy for cardiac diseases
  申请人：Kowa Co., Ltd.

  公开号：US05576324A1

  公开（公告）日：1996-11-19

  A quinoline derivative represented by general formula (1), a medicinally acceptable salt thereof, and a remedy for cardiac diseases containing the same: ##STR1## [wherein ring A represents a furan, dihydrofuran or dioxolane ring, and R.sup.1 represents an aminoalkyl group]. The compound (1) has a positively inotropic effect on myocardia and an antiarrhythmic effect, and can dilate blood vessels without extremely increasing the heart rate. Therefore, a remedy for cardiac diseases containing the same as the active ingredient is remarkably useful for treating cardiac insufficiency, arrhythmia, and so forth.

  一种以一般式（1）表示的喹啉衍生物，其药学上可接受的盐，以及含有该物质的心脏疾病疗法：##STR1## [其中环A代表呋喃、二氢呋喃或二氧杂环戊烷环，R.sup.1代表氨基烷基基团]。化合物（1）对心肌具有正性肌力作用和抗心律失常作用，并且可以扩张血管而不会极大增加心率。因此，含有该物质作为活性成分的心脏疾病疗法对治疗心脏功能不全、心律失常等疾病非常有用。
• QUINOLINE DERIVATIVE OR SALT THEREOF AND REMEDY FOR CARDIAC DISEASES CONTAINING THE SAME
  申请人：KOWA CO. LTD.

  公开号：EP0638571A1

  公开（公告）日：1995-02-15

  A quinoline derivative represented by general formula (1), a medicinally acceptable salt thereof, and a remedy for cardiac diseases containing the same, wherein ring A represents a furan, dihydrofuran or dioxolane ring, R¹ represents hydroxy, carboxy, alkoxycarbonyl, etc., R²s may be the same or different from each other and each represents hydrogen, alkyl, etc., R³ and R⁴ may be the same or different from each other and each represents hydrogen, halogen, alkyl, amino, alkoxy, etc., R⁵, R⁶, R⁷ and R⁸ may be the same or different from one another and each represents hydrogen or alkyl, m represents an integer of 0 to 3, and symbol ...... means that there may be a double bond formed by R⁶ and R⁸. The compound (1) has a positively inotropic effect on myocardia and an antiarrhythmic effect and can dilate blood vessels without extremely increasing the heart rate. Therefore, a remedy for cardiac diseases containing the same as the active ingredient is remarkably useful for treating cardiac insufficiency, arrhythmia, and so forth.

  一种由通式(1)代表的喹啉衍生物、其药用盐以及含有该衍生物的治疗心脏病的药物，其中环A代表呋喃、二氢呋喃或二氧戊环，R¹代表羟基、羧基、烷氧羰基等，R²s可以相同或不同，各自代表氢、烷基等、R³ 和 R⁴ 可以相同或互不相同，各自代表氢、卤素、烷基、氨基、烷氧基等，R⁵、R⁶、R⁷ 和 R⁸ 可以相同或互不相同，各自代表氢或烷基，m 代表 0 至 3 的整数，符号 ...... 表示 R⁶ 和 R⁸ 可以形成双键。化合物(1)对心肌具有正性肌力作用和抗心律失常作用，并能扩张血管而不会极度增加心率。因此，以该化合物为有效成分的心脏疾病治疗药物对治疗心功能不全、心律失常等有显著作用。
• [EN] SUBSTITUTED PYRIMIDONE DERIVATIVE, AND PHARMACEUTICAL COMPOSITION AND MEDICAL USE THEREOF<br/>[FR] DÉRIVÉ DE PYRIMIDONE SUBSTITUÉ, COMPOSITION PHARMACEUTIQUE ET UTILISATION MÉDICALE DE CELUI-CI<br/>[ZH] 取代的嘧啶酮衍生物、其药物组合物及医药上的用途
  申请人：[en]SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO., LTD.;[zh]上海海雁医药科技有限公司

  公开号：WO2023125812A1

  公开（公告）日：2023-07-06

  涉及取代的嘧啶酮衍生物、其药学上可接受的盐、立体异构体、药物组合物以及医药上的用途。所述取代的嘧啶酮衍生物为具有式(I)所示的结构的化合物，所述化合物具有显著的CSF-1R选择性抑制活性，十分具有实用价值。
• US5576324A
  申请人：——

  公开号：US5576324A

  公开（公告）日：1996-11-19
• Novel positive inotropic agents: synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives
  作者：Takafumi Fujioka、Shuji Teramoto、Toyoki Mori、Tetsumi Hosokawa、Takumi Sumida、Michiaki Tominaga、Youichi Yabuuchi

  DOI：10.1021/jm00098a003

  日期：1992.10

  A series of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinones has been synthesized and evaluated for positive inotropic activity on the canine heart. Some of these derivatives have a potent activity with none or negative chronotropic effect in isolated, blood-perfused dog heart preparations. They also display a high selectivity for positive inotropic effect over chronotropic and vasodilatory effects in anesthetized dogs. (+/-)-6-[2-Hydroxy-3-[(3-methoxybenzyl)amino]propoxy]-2(1H)-quinolinone (39) and (+/-)-6-[3-(3,4-dimethoxybenzyl)amino]-2-hydroxypropoxy]-2(1H)-quinolinone (40) were further investigated in conscious dogs. After iv administration, they did not affect heart rate or mean blood pressure at the dose producing a 50% increase in the peak of the first derivative of the left ventricular pressure. The compounds (39,OPC-18750, and 40,OPC-18790) are the most promising agents with desirable biological activities, and now are currently undergoing clinical evaluation.